1-(4-chlorophenyl)-2-methyl-4,5-dihydro-1H-imidazole | 1372812-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-chlorophenyl)-2-methyl-4,5-dihydro-1H-imidazole
• 英文别名: 1-(4-Chlorophenyl)-2-methyl-4,5-dihydroimidazole
• CAS: 1372812-21-9
• 化学式: C₁₀H₁₁ClN₂
• 分子量: 194.664
• InChiKey: QRFDCFGTOAERST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-2-methyl-4,5-dihydro-1H-imidazole 在 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以67%的产率得到N-(4-chlorophenyl)-N'-ethylethylenediamine
  参考文献：
  名称：

  Synthesis and Synthetic Applications of 1-Aryl-2-alkyl-4,5-dihydro-1H-imidazoles

  摘要：

  An easy synthesis of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles 1 by cyclo-condensation of N-acyl-N'-arylethylenediamines 2 is described. Such precursors were synthesized by aminolysis of the corresponding N-(2-bromoethyl)amides 3. Cyclizations were performed using trimethylsilyl polyphosphate as a mild dehydrating agent, under microwave irradiation. Chemical properties of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles, typical of the amidine system, were studied. Reduction of dihydroimidazoles with sodium cyanoborohydride leads regiospecifically to N-alkyl-N'-arylethylenediamines 4, and nucleophilic attack to methyl iodide leads to the corresponding 1-aryl-2-alkyl-3-methyl-4,5-dihydro-1H-imidazolium salts 5.

  DOI：

  10.1080/00397911.2011.552155
• 作为产物：
  描述：

  N-acetyl-N'-(4-chlorophenyl)ethylenediamine 在 trimethylsilyl polyphosphate 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以83%的产率得到1-(4-chlorophenyl)-2-methyl-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  Synthesis and Synthetic Applications of 1-Aryl-2-alkyl-4,5-dihydro-1H-imidazoles

  摘要：

  An easy synthesis of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles 1 by cyclo-condensation of N-acyl-N'-arylethylenediamines 2 is described. Such precursors were synthesized by aminolysis of the corresponding N-(2-bromoethyl)amides 3. Cyclizations were performed using trimethylsilyl polyphosphate as a mild dehydrating agent, under microwave irradiation. Chemical properties of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles, typical of the amidine system, were studied. Reduction of dihydroimidazoles with sodium cyanoborohydride leads regiospecifically to N-alkyl-N'-arylethylenediamines 4, and nucleophilic attack to methyl iodide leads to the corresponding 1-aryl-2-alkyl-3-methyl-4,5-dihydro-1H-imidazolium salts 5.

  DOI：

  10.1080/00397911.2011.552155

文献信息

• Copper-Catalyzed <i>N</i>-Arylation of 2-Imidazolines with Aryl Iodides
  作者：Owen A. Davis、Matthew Hughes、James A. Bull

  DOI：10.1021/jo400120r

  日期：2013.4.5

  The first copper-catalyzed N-arylation of 2-imidazolines is described. The reaction affords compounds with desirable lead-like characteristics in high yield with practical simplicity under inexpensive, "ligand-free" conditions. The cross coupling was successful with electron-rich and electron-poor aromatic iodides. Substrates bearing halides, esters, nitriles, and free hydroxyls are well tolerated, providing reactive handles for further functionalization, as are pyridines. In addition, the regioselective N-arylation of a 4-substituted imidazoline is reported.
• Spherical CuO Nanoparticles as Catalyst for Chan–Lam Cross-Coupling Reaction under Base Free Condition
  作者：Sameeran Kumar Das、Pangkita Deka、Monikha Chetia、Ramesh C. Deka、Pankaj Bharali、Utpal Bora

  DOI：10.1007/s10562-017-2278-z

  日期：2018.2

  An easy methodology has been developed for the N-arylation of imidazole with arylboronic acid in absence of base and ligand with the aid of as-synthesized CuO nanoparticles. The CuO nanoparticles have been synthesized via precipitation route. The as-synthesized copper oxide nanoparticles are well characterized by various analytical and spectroscopic techniques, such as powder XRD, Raman spectroscopy, TEM and BET surface area analyses. The CuO nanoparticles appear as spherical in shape with a surface area of 15.4 m(2)/g. The mentioned reaction successfully proceeds at moderate temperature in presence of the as-synthesized nanoparticles. The protocol is applicable to a wide variety of electronically diverse precursor moieties signifying its well applicability.Graphical Abstract[GRAPHICS].